Pirate Captain Calico Jack was born John Rackham, on the 21st of December, 1682 in Jamaica. He was active during the end of the “golden age of piracy” in the 18th century and operated in Bahamian waters.

We remember Captain Calico Jack for two main reasons: his design of the Jolly Roger Flag and his two female crew members.

“Jolly Roger” is the term applied to the various flags flown on pirate ships to identify its crew as pirates. The Jolly Roger flag most associated as a pirate flag is the standard skull and cross bones design where the skull of a human rests above two longer bones arranged in an X. History reports that the flag was used as a symbol of terror and intimidation. Pirates hoped the flags would communicate that they were not afraid to break the traditional rules of engagement, forcing the victims to surrender without a fight.

The flag has other meanings today, such as a signifier of hazardous or poisonous elements.

Calico Jack is also remembered for his two female crew members, Anne Bonny and Mary Read. Anne Bonny was the wife of sailor James Bonny, employed by Governor Rogers. Calico Jack had an affair with Anne Bonny and when her husband, James Bonny discovered the affair, he brought her to the Governor to be punished. The pirate Captain offered to buy Anne in a divorce agreement but she refused. Anne related the proposal to the treatment of an animal and she refused to be treated as one. Calico Jack and Anne escaped with the other crew members in a stolen sloop that belonged to John Ham. They sailed for two months on the Caribbean where they attacked other ships, inviting the crews to join them. It is during an attack that Calico Jack met Mary Read and did not recognize Read’s hidden gender.

The reign of Calico Jack came to an end when he was captured in September of 1720, after his ship was attacked by a sloop sent by Governor Nicholas Lawes. Calico Jack and his crew were brought back to Jamaica where they were sentenced to be hanged. Mary Read died of a fever related to pregnancy complications and Anne Bonny was pardoned due to pregnancy.

Calico Jack’s legacy is remembered in Disney’s “Pirates of the Caribbean: The Curse of the Black Pearl”. He is depicted in the film’s opening scene when Jack Sparrow sails into Port Royal and passes a sign, “Pirates, Ye Be Warned” hanging next to the skeletal remains of a pirate meant to represent the dead captain. The Black Pearl also proudly flies Calico Jack’s design of the Jolly Roger flag.